95687-41-5

Basic information

• Product Name: Z-TRANS-4-HYDROXY-L-PROLINOL
• Synonyms: CBZ-TRANS-4-HYDROXY-L-PROLINOL;(2S,4R)4-Hydroxy-2-(hydroxymethyl)pyrrolidine, N-CBZ protected;1-CBZ-TRANS-4-HYDROXY-L-PROLINOL;N-CBZ-TRANS-4-HYDROXY-L-PROLINOL;TRANS-N-CBZ-4-HYDROXY-L-PROLINOL;Trans-N-benzyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine;Z-Hyp-Ol;Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS NO: 95687-41-5
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.27838
• Product Categories: Amino Acid Derivatives;Amino Acid Derivatives;Amino Alcohols;Peptide Synthesis
• Mol File: 95687-41-5.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 240 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.297 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.68E-08mmHg at 25°C
• Refractive Index: n20/D 1.547(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.56±0.40(Predicted)
• CAS DataBase Reference: Z-TRANS-4-HYDROXY-L-PROLINOL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-TRANS-4-HYDROXY-L-PROLINOL(95687-41-5)
• EPA Substance Registry System: Z-TRANS-4-HYDROXY-L-PROLINOL(95687-41-5)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 95687-41-5(Hazardous Substances Data)

Usage

General Description

Z-TRANS-4-HYDROXY-L-PROLINOL, also known as Z-L-Hyp-OH, is a chemical compound that belongs to the class of proline derivatives. It is a white crystalline powder that is soluble in water and alcohols. Z-TRANS-4-HYDROXY-L-PROLINOL is commonly used as a chiral auxiliary in organic synthesis, especially in the asymmetric synthesis of pharmaceuticals and other biologically active compounds. It has also been utilized as a catalyst for enantioselective organic reactions. Additionally, Z-TRANS-4-HYDROXY-L-PROLINOL has shown potential as a reagent for the determination of chiral acids and as a building block in the synthesis of complex organic molecules.

InChI:InChI=1/C13H17NO4/c15-8-11-6-12(16)7-14(11)13(17)18-9-10-4-2-1-3-5-10/h1-5,11-12,15-16H,6-9H2/t11-,12+/m0/s1

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 
• 209269-34-1 N-CBZ-L-hydroxyproline 
• 197079-48-4 trans-N-(Benzyloxycarbonyl)-4-hydroxy-L-proline 

Downstream Products

• 95687-42-6 (2S,4R)-benzyl 4-(tosyloxy)-2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 260417-93-4 benzyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidine-1-carboxylate 
• 500733-24-4 (2S,4R)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxypyrrolidine 
• 847994-39-2 ethyl 3-[(2S,4S)-2-(tert-butoxycarbonylaminomethyl)-4-(N³-benzoyl-thymin-1-yl)-pyrrolidin-1-yl]-propanoate 
• 847994-48-3 (2S,4R)-N₁-(benzyloxycarbonyl)-4-hydroxy-2-(aminomethyl)-pyrrolidine 
• 847994-45-0 (2S,4R)-N₁-(benzyloxycarbonyl)-4-hydroxy-2-(azidomethyl)-pyrrolidine 
• 847994-36-9 (2S,4R)-N₁-(benzyloxycarbonyl)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxy-pyrrolidine 
• 232931-63-4 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole] 
• 260417-96-7 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] 
• 260417-95-6 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-nitro-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] 
• 260417-98-9 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine] 
• 260417-97-8 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] 
• 260418-24-4 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-t-butyldimethylsilyloxymethyl-4-methylidene-2,3-dihydropyrrole] 
• 260418-26-6 1,1'-[[(pentane-1,5-diyl)dioxy]-bis[(2-amino-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine] 

Relevant articles and documents

Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate

A gram-scale synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino acid residue, is presented. A pivotal transformation in the route involves an intramolecular hydrosilylation-oxidation sequence to set the ring-fusion stereocenters of the bicyclic scaffold. Other notable features of the synthesis include a high-yielding, highly diastereoselective alkylation of a pseudoephenamine amide, a convergent sp3-sp2 Negishi coupling, and a one-pot transacetalization-reduction reaction to form the target compound's oxepane ring. Implementation of this synthetic strategy has provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.

FUSED HETEROCYCLIC BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

Scale-up Synthesis of Tesirine

This work describes the enabling synthesis of tesirine, a pyrrolobenzodiazepine antibody-drug conjugate drug-linker. Over the course of four synthetic campaigns, the discovery route was developed and scaled up to provide a robust manufacturing process. Early intermediates were produced on a kilogram scale and at high purity, without chromatography. Midstage reactions were optimized to minimize impurity formation. Late stage material was produced and purified using a small number of key high-pressure chromatography steps, ultimately resulting in a 169 g batch after 34 steps. At the time of writing, tesirine is the drug-linker component of eight antibody-drug conjugates in multiple clinical trials, four of them pivotal.